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Book reviews
Organometallics in Synthesis; A Manual
M. Schlosser (ed)
Wiley, Chichester, UK, 1994
614 pp. f60 (UK), $95 (USA)
ISBN 0-471-93637-5
There are by now many texts describing the use of
organometallic compounds in synthesis. Most restrict
themselves to an overall description of reaction types
and synthetic possibilities. Few go the extra mile and
include actual experimental recipe details of how to do
the synthesis. To its credits this book does that, and this
extra feature makes the book particularly useful in its
class. The experimental details are given in full,
together with a reference to the original literature
source. Accompanying the experimental details are
numerous discussions of practical handling and safety
aspects of the work. So as a book of recipes, this work
has value in itself.
What adds an extra dimension is the combination of
the experimental details with the descriptive sections
where the history, scope, variety and limitations of the
particular reaction type are discussed. Many of the
most important synthetic organometallics are covered,
namely organoalkali reagents (M. Schlosser), titanium
(M. T. Reetz), organocopper reagents (B. H.
Lipschutz), palladium (L. S. Hegadus), organoboron
chemistry (K. Smith), organoaluminium componds (H.
Yamamoto) and organotin chemistry (H. Nozaki). The
chapter on the industrial applications of organolithium
compounds. (F. Totter and P. Rittmeyer) does not
contain experimental details. These are covered in the
chapter by Schlosser, however.
Although the experimental details are reproduced in
detail and, as the editor notes, the co-authors have
‘shared their expertise with the reader’, there is no
claim that the syntheses would have been personally
verified by the individual authors. With only nine
authors, this would seem to be impossible. However,
this would not detract from the usefulness of the book
as all are very experienced in the practical use of the
synthesis types they describe. There are numerous
references to chiral synthetic work in the text.
The chapters are sufficiently referenced (Chapter 1,
126; Chapter 2, 55; Chapter 3, 328; Chapter 4, 172;
Chapter 5, 168; Chapter 6, 103; Chapter 7,52; Chapter
8, 183). The subject index occupies 16i pages. The
formula index covers about 400 compounds. The experimental descriptions are not presented in uniform quantity but, by way of example, the chapter on titanium in
synthesis has 48 experimental descriptions, that on
organocopper 124 experiments, palladium chemistry
has 19, organoboron 41, aluminium a disappointing 3,
tin 9, alkali metals 67. Clearly the coverage is not
uniform, but the totality of the synthetic procedures
described makes this a very useful handbook in the
CCC 0268-2605/95/08072 1-02
01995 by John Wiley & Sons, Ltd.
areas with which it is concerned. It is disappointing that
there are no chapters on magnesium species, nor on
Group IIB (Group 12) or on the use of organotransition metals generally. There is still room for a companion volume.
At f60 (UK) I cannot rate this as an over-expensive
book. Indeed, I might propose that the proud parents
of newly enrolled Ph.D. students in the area consider
making a personal copy of this book as a gift to their
offspring as they embark on their research careers. I
rate this a useful starter pack for new researchers. I also
believe that research groups would benefit from holding a laboratory copy. The book should be a standard
text for organometallic libraries.
De Montjfort University, Leicester, U K
Inorganic Experiments
J. Derek Woollins (ed)
VCH, Weinheim, 1994
ISBN 0-527-29253-5 (hardback);
0-527-29235-7 (paperback)
Over the years our department has built up a large
collection of undergraduate experiments in inorganic
chemistry. Even so, we are always eager to find new
ones and the appearance of this well-produced text is
therefore very welcome. The stated aim of the editor,
J. Derek Woollins, is to provide ‘meaningful experiments which develop laboratory skills, introduce interesting chemistry and are reliable and not always easy to
find’. Those goals are achieved in some at least of the
65 (or so) experiments. With some 70 authors there are
the expected variations in style and the amount of
information provided. Each experiment is said to have
been tested by the contributing author(s); however, the
editor does add the disclaimer ‘. . . so we can optimistically assume that they “work” . . .’! He has subdivided
the experiments into ‘introductory’, ‘intermediate’ and
‘advanced’. This classification should only be taken as a
rough guide; for example experiment 2.11 on the preparation of two phosphate esters (not identified) and the
use of their ‘H and 31PNMR spectra for identification
would seem, to me at least, to be too difficult as an
introductory experiment. A fair number of the experiments have appeared in older inorganic texts and have
certainly been in our collection for at least 20 years,
e.g. experiments 2.1 (preparation and investigation of
some co-ordination compounds), 2.4 (copper oxalate)
and 2.7 (linkage isomerism). The method of preparation of ferrocene and its acetylation (3.1) are longestablished procedures used in most courses (incidentally, we find that using half the quantities advocated is
more than sufficient).
My one major criticism is the lack of information
accompanying a large number of the experiments, i.e.
the aims of the experiment, the time required, the
expected yields and any likely pitfalls-essential information for laboratory instructors.
My recommendations are that all who teach inorganic chemistry should make use of this text and that
we should inform the editor of the success or otherwise
of the experiments we try.
De Montfort University, Leicester, U K
Dictionary of Organometallic Compounds
B. J. Aylett, M. F. Lappert and P. L. Pauson (eds)
Chapman and Hall, London
f2950 (hardback). f3500 CD ROM (single user).
f8750 CD ROM (network).
ISBN 0 412 43060 6 (five-volume set)
The first edition of this well-known reference work was
published in three volumes in 1984, and the same
editors have now expanded the text to five volumes in
the 1995 second edition. A feature of this edition will
be the issue of a regular series of updates of new
compounds or data from mid-1995 in either hard copy
or CD-ROM form. Researchers are also invited to send
details of new compounds or groups of compounds to
the Editors for possible inclusion.
The original concept of the Dictionary was to provide
‘a well organised compendium of essential facts on
selected organometallic compounds’ and the Editors
believe that this ‘has been shown to fulfil a real need
amongst chemists’. This, together with the manifest
expansion of the field over the last ten years, has lead to
the second edition. Each entry has been revised and
updated, with a further focus on synthetic routes,
including a new index of synthetic reagents. The present edition contains more than 10 000 extra entries over
the first edition, making a total of over 40 000.
The format of the Dictionary is well known to organometallic chemists. The essential feature is the ordering of compounds in element sections by alphabetical
listing of the metallic element. Within each section the
arrangement of entries is in order of molecular formula
using the Hill convention (i.e. C, H and then the
remaining elements in alphabetical sequence of chemical symbol).
Compounds containing more than one metal are
cross-referenced. Each entry contains essential physical
details about the compound and also the CAS number.
A series of literature references is then given which
includes a brief description of the main thrust of that
reference (e.g. synth., use, pmr, uv, etc.). Each entry is
also numbered at the point of entry to assist searching.
Volume 5 includes the three indexes: an index of
synthetic reagents, a molecular formula index in Hill
convention order and a CAS Registry number index in
serial order. Although the Dictionary does not claim to
be a comprehensive source on hazard data, such information is given briefly in a proportion of entries. Each
element section also provides a structure index.
In the view of this Reviewer, the Dictionary is an
essential resource for the library of a Department
specializing in organometallic chemistry at the research
or undergraduate level. The cost probably makes this
the only location where the volumes will be available.
The Dictionary is now also available on CD ROM, at
a cost of f3500 for a single user and f8”50 for a network
version. In any event, the Dictionary is an invaluable
source of information to the organometallic chemist
and access to it is essential.
De Montfort University, Lvicester LEI 9BH
PO Box 143
Organic Syntheses, Volume 72
D. L. Coffen (ed)
Wiley, New York, 1995
f36.95 (UK)
ISBN 0 471 30727 0
The first volume of the series Organic Syntheses was
published in 1921; Roger Adams was Editor-in-Chief.
The subtitle says it all: “an annual publication of
satisfactory methods for the preparation of organic
chemicals.’ The current volume is the 72nd: the length
of the publishing run and the vigour arid rigour shown
in its production attest to the continuing need for this
series and its popularity.
Many of the 32 syntheses detailed in Vol. 72 employ
organometallic reagents, reflecting thc current trend,
and it is not unreasonable to view much of the methodology as applied organometallic chc mistry. Specific
examples include:
(1) the asymmetric hydrogenation of allylic alcohols
using BINAP-ruthenium complexes: the preparation of IS}-{-}-citronello1 from. geraniol. The
preparation of the catalyst is given although the
word ‘catalyst’ hardly appears in the description.
(2) The rearrangement of trans-stilbene to diphenylacetaldehyde with methylaluminiiimbis(4-bromo2,6-di-tert-butylphenoxide) (MABE) as catalyst.
(3) The synthesis of functionalized enynes by
palladium/copper-catalysed coupling reactions.
(4) The use of highly reactive calciuoi for the preparation of organocalcium reagents.
( 5 ) The use of tributyltin hydride in the stereoslective
synthesis of 2,2-disubstituted 1-fluaroalkenes.
( 6 ) The use of Me3SiCF3 in the synthesis of
(7) The preparation of a water-soluble tin hydride, tris
The dedicated team of submitters and checkers
appears to have done their commendabl: best to ensure
clarity in the text. The publishers are 10 be congratulated in making available to members of various chemical societies this volume and some preceding ones (Vol.
62 onward) in an inexpensive soft-cover edition.
Hard-cover versions and their indexes should be part of
all libraries.
Vancouvtr, BC, Canada
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